Best Kids Chapter Books About Choosing cheeriness

Top 5 Books to Teach Your Children to Choose Happiness

Updated Feb. 26, 2019

We all tell our children that happiness is a choice, and here are the books to help you prove it! We've compiled a list of our favorite 30 books that exemplify choosing cheeriness, because this lesson is never too early to learn, and you can never have too many reminders. It's hard to learn to regulate your emotions (just ask any two-year-old!), and if we're being honest, it's something we're even mastering as adults. These books are great way to learn and reinforce the knowledge that we control our emotions, no matter our circumstances. To quote Leo Tolstoy, "If you want to be happy, be."

After losing her parents, young Mary Lennox is sent from India to live in her uncle’s gloomy mansion on the wild English moors. She is lonely and has no one to play with, but one day she learns of a secret garden somewhere in the grounds that no one is allowed to enter. Then Mary uncovers an old key in a flowerbed – and a gust of magic leads her to the hidden door. Slowly she turns the key and enters a world she could never have imagined.

Born with a facial deformity that initially prevented his attendance at public school, Auggie Pullman enters the fifth grade at Beecher Prep and struggles with the dynamics of being both new and different, in a sparsely written tale about acceptance and self-esteem.

I love these stories based off of the original Winnie the Pooh, and love that it's divided up into four stories with the four seasons. Pooh is always so positive and looks for the good in everything, there's so much wisdom from the little sayings throughout the story. I think Pooh is a great example of choosing to look at the bright side and be happy. :) Plus, I was surprised by how high quality this book is! The illustrations throughout are also gorgeous.

For the 90th anniversary of Winnie-the-Pooh, a sequel featuring new stories and a new character from the Hundred Acre Wood.
Now a New York Times Bestseller.
The Trustees of the Pooh Properties have commissioned four authors to write in the timeless style of A.A. Milne to create a quartet of charming new adventures for Winnie-the-Pooh, Christopher Robin, and their friends. Winter, Spring, Summer, and Fall: take a trip back to the Hundred Acre Wood with a collection of tales sure to delight year-round.
One story finds Winnie-the-Pooh and Piglet on a quest to discover the "Sauce of the Nile" (they suspect it's apple). And in another, all the animals rally around poor Eeyore when he thinks he sees another donkey eyeing his clover. The winter story features a new penguin character, based on a stuffed toy owned by Christopher Robin Milne himself. Readers of all ages will love rediscovering old friends and making new ones in this essential new volume of Pooh stories.
The book feature beautiful color artwork in the style of Ernest H. Shepard by Mark Burgess.

Even though sometimes "it's a hard-knock life," Annie shows that you can choose to be happy and believe "the sun will come out tomorrow!"

It's a hard-knock life for America's favorite orphan! Everyone knows the story of the irrepressible Annie, who lives at Miss Hannigan's orphanage until she beats the odds and finds a new life with the benevolent and wealthy Daddy Warbucks. Annie has enchanted millions of readers from her original comic strip appearance to the hit Broadway musical. Now, with a Tony-nominated revival playing on Broadway, Puffin is reissuing this novelization of the classic story, with a new introduction by Tony and Emmy Award-winning author Thomas Meehan. This is an adaptation that delves even deeper into Annie's story, as she lives on the streets during the Great Depression, finds Sandy the dog, and encounters characters both familiar and new.

Fifth grader Annie is just like every other girl in her small suburban town. Except she's starting to realize that she isn't.
Annie is the youngest of nine children. Instead of being condemned to the bottom of the pecking order, she wants to carve out place for herself in the world. But it’s hard to find your destiny when the only thing you’re good at is being cheerful. Annie is learning that it’s difficult to be Annie, period, and not just because her clothes are worn-out hand-me-downs, and she suffers from a crippling case of dyslexia, but also because there are secrets in her life no one in her family is willing to face.
In Snow Lane, Josie Angelini presents a story about a resilient girl who, in spite of many hardships, can still find light in the darkest of places.